8,9-Dichloro-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole → HCID 59075499、化合物

HRID 1356364ノート

反応式

HRID 1356364 の反応式
[Cl:1][C:2]1[C:3]([Cl:16])=[CH:4][C:5]2[C:6]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11][C:7]=3[NH:8][C:9]=2[CH:10]=1>C(O)(C(F)(F)F)=O.CO>[Cl:1][C:2]1[C:3]([Cl:16])=[CH:4][C:5]2[C@@H:6]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11][C@@H:7]3[NH:8][C:9]=2[CH:10]=1

参加物

4

反応物 1

HCID 226092048,9-Dichloro-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

生成物 1

HCID 59075499HCID 59075499、化合物収率 36%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

A solution of 8,9-dichloro-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.40 g, 1.6 mmol) in TFA (4.0 mL) was cooled to 0° C., then a freshly prepared solution of Na(CN)BH3 (0.49 g, 7.8 mmol) in MeOH (1.5 mL) was added dropwise. The ice bath was removed after the addition was complete. After 2.5 h, the reaction was diluted with H2O, made basic with 50% aqueous NaOH, and extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, decanted, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography and prep HPLC to give 0.14 g (36%) of the title compound as pale orange solid. 1H NMR (d-CHCl3) δ 7.00, 6.58, 4.22, 3.81, 3.58, 3.14-2.98, 2.79, 2.07-1.87; IR (drift) 3201, 3170, 3149, 3031, 2927, 2852, 2838, 2750, 1608, 1483, 1450, 1365, 1273, 832, 660 cm−1; HRMS (FAB) calcd for C12H14Cl2N2+H 257.0612, found 257.0614.

後処理

  1. customThe ice bath was removed
  2. additionafter the addition
  3. additionthe reaction was diluted with H2O
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by silica gel chromatography and prep HPLC

出典と根拠

ORDレコード
ord-293e043037634de0a1d4a54e5acfda66
出典データセット
uspto-grants-2003_07
特許番号
US06586421B2

反応ノート

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